Holiday Homes in The Berkshires

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Next weekend
10 Oct - 12 Oct
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17 Oct - 19 Oct
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31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Holiday Homes in The Berkshires and around

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (148)
"We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved."
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Stockbridge Village in Summer
Dining

Stockbridge Village in Summer

9.0 out of 10, Wonderful, (18)
"This is a great home within walking distance of the interesting town of Stockbridge. The place is well equipped and has a charm consistent of what you can expect for a historic farm house. We would stay here again."
Stockbridge Village in Summer
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Fridge, microwave, oven, stovetop

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

10.0 out of 10, Exceptional, (37)
"We had the most wonderful trip! The location is perfect - easy access to downtown GB but still very relaxing and private. The kitchen is beautifully equipped and we ended up cooking most of our meals there. And the living room/great room led to hours of conversation. Can't wait to come back for a longer stay."
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is €693
includes taxes & fees
6 Oct - 7 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.
Contemporary Berkshire Home with Views of Taconic Golf Course
Smart TV, fireplace, DVD player, books

Contemporary Berkshire Home with Views of Taconic Golf Course

10.0 out of 10, Exceptional, (8)
"Lovely property. Well kept house, nicely decorated. Very much enjoyed our stay."
Contemporary Berkshire Home with Views of Taconic Golf Course
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
Interior

Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location

9.6 out of 10, Exceptional, (72)
"Beautiful house and location that was perfect for a family weekend. Would 100% recommend!"
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
General Williams Estate House Lenox/Stockbridge
Exterior

General Williams Estate House Lenox/Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (110)
"The house was beautiful, the outdoor space was gorgeous, and the pool was amazing! I highly recommend this charming spot."
General Williams Estate House Lenox/Stockbridge
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is €439
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (25)
"We had a wonderful time in this home. It accommodated our family of 4 easily. Several of us had to work the first day there and there were ample quiet spots and quality wifi for us. So easy to walk to town to restaurants etc"
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Hearts Desire is a furnished whole house in a small, colorful garden center.
Exterior detail

Hearts Desire is a furnished whole house in a small, colorful garden center.

10.0 out of 10, Exceptional, (93)
"This was our third time at this property. We still love it and look forward to returning again."
Hearts Desire is a furnished whole house in a small, colorful garden center.
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Lake

Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++

9.4 out of 10, Exceptional, (60)
"I had such a great stay with a bunch of friends at the Fox Hollow Estate. The house is exactly as described, and very spacious. At no point did I ever feel packed into the house, there are so many activities that you can do around the area. If you're visiting for foliage, the property has wonderful viewpoints and is within a close 20 or less minute drive to the best views. I would gladly stay at the place again if I was in the area."
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Smart TV, fireplace, DVD player

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Exterior

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (21)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (73)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
Fridge, microwave, oven, stovetop

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
The Meadows House @ Otis Ridge w/ 7-person hot tub
Outdoor spa tub

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub
A Grand property in Historic Stockbridge
Fridge, microwave, oven, stovetop

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (102)
"The Taggart House was a wonderful place to gather with friends and family to celebrate my birthday. The house is beautiful; the rooms are large; kitchen is great; bugs kept us from hanging out in the backyard but the conservatory was light and bright and a perfect spot for cocktails. We loved the proximity to the town of Stockbridge and we would walk back and forth a couple times a day. We had a couple of small issues, and Caitlin was very responsive in answering my questions/concerns. All in...
A Grand property in Historic Stockbridge
Art House! Spacious Getaway By Mass Moca
Dining

Art House! Spacious Getaway By Mass Moca

10.0 out of 10, Exceptional, (12)
"This house was just perfect for us! So cozy and beautiful. "
Art House! Spacious Getaway By Mass Moca
Stockbridge Village Cottage With Mountain View’s and walk to town
Outdoor dining

Stockbridge Village Cottage With Mountain View’s and walk to town

9.8 out of 10, Exceptional, (63)
"Perfect long weekend with family at this lovely home!"
Stockbridge Village Cottage With Mountain View’s and walk to town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Beautiful well-maintained property. Very clean every possible convenient you could want. Friendly welcoming staff plan to return to this property often."
Craig 1-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Find out more about The Berkshires

Find out more about The Berkshires

The Berkshires Holiday Homes information

Number of reviews
816
Accommodation
330 Holiday Homes
Lowest Price
€439
Highest Price
€693

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